Search Cheap Flights to
Windsor

Photo by William E Berry Jr.

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Windsor Flights as Low as $405

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

JetBlue Airways
Thu, Jun 26 - Fri, Jul 4
RIC
Richmond Intl.
LEB
Lebanon Municipal
$405 Roundtrip, found 3 days ago
$405
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Thu, Jun 26 from Richmond Intl. to Lebanon Municipal, returning Fri, Jul 4, priced at $405 found 3 days ago
JetBlue Airways
Fri, Jun 27 - Tue, Jul 1
RIC
Richmond Intl.
LEB
Lebanon Municipal
$413 Roundtrip, found 3 days ago
$413
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Fri, Jun 27 from Richmond Intl. to Lebanon Municipal, returning Tue, Jul 1, priced at $413 found 3 days ago
JetBlue Airways
Fri, Jun 27 - Sat, Jun 28
RIC
Richmond Intl.
LEB
Lebanon Municipal
$423 Roundtrip, found 3 days ago
$423
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Fri, Jun 27 from Richmond Intl. to Lebanon Municipal, returning Sat, Jun 28, priced at $423 found 3 days ago
JetBlue Airways
Sun, Jun 29 - Wed, Jul 2
RIC
Richmond Intl.
LEB
Lebanon Municipal
$433 Roundtrip, found 2 days ago
$433
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sun, Jun 29 from Richmond Intl. to Lebanon Municipal, returning Wed, Jul 2, priced at $433 found 2 days ago
JetBlue Airways
Thu, Jun 26 - Mon, Jun 30
RIC
Richmond Intl.
LEB
Lebanon Municipal
$435 Roundtrip, found 3 days ago
$435
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Thu, Jun 26 from Richmond Intl. to Lebanon Municipal, returning Mon, Jun 30, priced at $435 found 3 days ago
JetBlue Airways
Thu, Jun 26 - Mon, Jun 30
RIC
Richmond Intl.
LEB
Lebanon Municipal
$441 Roundtrip, found 3 days ago
$441
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Thu, Jun 26 from Richmond Intl. to Lebanon Municipal, returning Mon, Jun 30, priced at $441 found 3 days ago
JetBlue Airways
Tue, Jun 24 - Sat, Jun 28
RIC
Richmond Intl.
LEB
Lebanon Municipal
$441 Roundtrip, found 3 days ago
$441
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Jun 24 from Richmond Intl. to Lebanon Municipal, returning Sat, Jun 28, priced at $441 found 3 days ago
JetBlue Airways
Wed, Jun 25 - Wed, Jul 2
RIC
Richmond Intl.
LEB
Lebanon Municipal
$456 Roundtrip, found 5 hours ago
$456
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Wed, Jun 25 from Richmond Intl. to Lebanon Municipal, returning Wed, Jul 2, priced at $456 found 5 hours ago
American Airlines
Sun, Jun 29 - Wed, Jul 2
RIC
Richmond Intl.
LEB
Lebanon Municipal
$459 Roundtrip, found 2 days ago
$459
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sun, Jun 29 from Richmond Intl. to Lebanon Municipal, returning Wed, Jul 2, priced at $459 found 2 days ago
Delta
Sun, Jun 29 - Wed, Jul 2
RIC
Richmond Intl.
LEB
Lebanon Municipal
$460 Roundtrip, found 2 days ago
$460
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Jun 29 from Richmond Intl. to Lebanon Municipal, returning Wed, Jul 2, priced at $460 found 2 days ago
American Airlines
Sun, Jun 29 - Wed, Jul 2
RIC
Richmond Intl.
LEB
Lebanon Municipal
$464 Roundtrip, found 2 days ago
$464
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sun, Jun 29 from Richmond Intl. to Lebanon Municipal, returning Wed, Jul 2, priced at $464 found 2 days ago
JetBlue Airways
Wed, Jun 25 - Mon, Jun 30
RIC
Richmond Intl.
LEB
Lebanon Municipal
$466 Roundtrip, found 2 hours ago
$466
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Wed, Jun 25 from Richmond Intl. to Lebanon Municipal, returning Mon, Jun 30, priced at $466 found 2 hours ago
Delta
Sun, Jun 29 - Wed, Jul 2
RIC
Richmond Intl.
LEB
Lebanon Municipal
$470 Roundtrip, found 2 days ago
$470
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Jun 29 from Richmond Intl. to Lebanon Municipal, returning Wed, Jul 2, priced at $470 found 2 days ago
JetBlue Airways
Wed, Jun 25 - Mon, Jun 30
RIC
Richmond Intl.
LEB
Lebanon Municipal
$472 Roundtrip, found 2 hours ago
$472
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Wed, Jun 25 from Richmond Intl. to Lebanon Municipal, returning Mon, Jun 30, priced at $472 found 2 hours ago
JetBlue Airways
Sun, Jun 29 - Wed, Jul 2
RIC
Richmond Intl.
LEB
Lebanon Municipal
$474 Roundtrip, found 2 days ago
$474
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sun, Jun 29 from Richmond Intl. to Lebanon Municipal, returning Wed, Jul 2, priced at $474 found 2 days ago
JetBlue Airways
Wed, Jun 25 - Mon, Jun 30
RIC
Richmond Intl.
LEB
Lebanon Municipal
$477 Roundtrip, found 2 hours ago
$477
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Wed, Jun 25 from Richmond Intl. to Lebanon Municipal, returning Mon, Jun 30, priced at $477 found 2 hours ago

Cheap Flights to Windsor

Fall in love at first flight with your vacation to Windsor by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Windsor on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Windsor, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Windsor

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Windsor with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the VSF airport.

What is the cheapest month to fly to Windsor?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Windsor are in June, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Windsor?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Windsor.

What airport is best to fly into Windsor?

When you’re planning your trip to Windsor, convenience is the name of the game. Luckily, Windsor Lebanon Municipal Airport is nearby so you can deplane and get going on checking off everything on your Windsor must-do list.

How much are flights to Windsor?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Windsor on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $405, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Windsor?

The trick to saving a stack of cash on your flight to Windsor? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $405 right now, why wait?

Windsor Flight Information
Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Roundtrip price
$405

Last Minute Hotel Deals in Windsor

Align Inn Vermont
Align Inn Vermont
2.5 out of 5
5817 Woodstock Rd, Quechee, VT
Book a stay at this business-friendly hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (1,007 reviews)
"A nice motel that didn’t feel like a motel. Good facilities and breakfast spread. Great location near the gorge and other sites as well as restaurants."

Reviewed on Jun 14, 2025

Get rates
Align Inn Vermont
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
Stay at this 4.5-star luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (519 reviews)
Stunning
"Always a stunning stay in Woodstock!"

Reviewed on Jun 2, 2025

Get rates
Woodstock Inn & Resort
Super 8 by Wyndham White River Junction
Super 8 by Wyndham White River Junction
2 out of 5
442 North Hartland Rd, I-91 Exit 11 Rt 5 S 1/4 Mile, White River Junction, VT
Book a stay at this business-friendly motel in White River Junction. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
6.4/10 (1,001 reviews)
"Stayed 3 nights and found it clean and friendly. Excellent access to highways, shopping and food. Room was clean and staff was super friendly. No problems."

Reviewed on Jun 9, 2025

Get rates
Super 8 by Wyndham White River Junction
Killington Mountain Lodge, Tapestry Collection by Hilton
Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 out of 5
2617 Killington Rd, Killington, VT
Stay at this 3.5-star ski hotel in Killington. Enjoy free WiFi, a free ski shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the ...
7.2/10 Good! (1,003 reviews)
"Nice stay"

Reviewed on Jun 10, 2025

Get rates
Killington Mountain Lodge, Tapestry Collection by Hilton
Hanover Inn Dartmouth
Hanover Inn Dartmouth
4 out of 5
Two East Wheelock Street, Hanover, NH
Stay at this 4-star luxury hotel in Hanover. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property condition ...
9.6/10 Exceptional! (832 reviews)
"Beautiful hotel, well appointed rooms, excellent restaurant, great location."

Reviewed on Jun 9, 2025

Get rates
Hanover Inn Dartmouth
Best Western West Lebanon-Hanover Hotel
Best Western West Lebanon-Hanover Hotel
2.5 out of 5
45 Airport Road, West Lebanon, NH
Book a stay at this business-friendly hotel in West Lebanon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (848 reviews)
"Easy access from 89. Check in was simple & friendly. Room was clean. Great value for half the price of the hotels next to DHMC."

Reviewed on Jun 12, 2025

Get rates
Best Western West Lebanon-Hanover Hotel
The Shire Woodstock
The Shire Woodstock
3 out of 5
46 Pleasant St., Woodstock, VT
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (757 reviews)
"property was great , small grocery store across the street very convenient. Everything in walking distance. Only negative was we arrived on a monday and most restaurants are closed."

Reviewed on Jun 13, 2025

Get rates
The Shire Woodstock
Hilton Garden Inn Hanover Lebanon
Hilton Garden Inn Hanover Lebanon
3 out of 5
35 Labombard Rd, Lebanon, NH
Stay at this 3-star business-friendly hotel in Lebanon. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
9/10 Wonderful! (1,002 reviews)
"Very comfy bed and quiet room. No noise from above, below or sides. Nice to have good, free coffee in the reception area every morning."

Reviewed on Jun 9, 2025

Get rates
Hilton Garden Inn Hanover Lebanon
See all 2,597 properties in Windsor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.